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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H33F3N2O5S
Molecular Weight 602.664
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIPRANAVIR

SMILES

CCC[C@@]2(CCC1=CC=CC=C1)CC(O)=C([C@H](CC)C3=CC=CC(NS(=O)(=O)C4=NC=C(C=C4)C(F)(F)F)=C3)C(=O)O2

InChI

InChIKey=SUJUHGSWHZTSEU-FYBSXPHGSA-N
InChI=1S/C31H33F3N2O5S/c1-3-16-30(17-15-21-9-6-5-7-10-21)19-26(37)28(29(38)41-30)25(4-2)22-11-8-12-24(18-22)36-42(39,40)27-14-13-23(20-35-27)31(32,33)34/h5-14,18,20,25,36-37H,3-4,15-17,19H2,1-2H3/t25-,30-/m1/s1

HIDE SMILES / InChI

Description

Tipranavir (PNU-140690, trade mark APTIVUS) is a potent, orally bioavailable nonpeptidic HIV protease inhibitor of the 5,6-dihydro-4-hydroxy-2-pyrone sulfonamide class. Tipranavir has potent in vitro activity against a variety of HIV-1 laboratory strains and clinical isolates, including those resistant to ritonavir, as well as HIV-2. The drug is launched in several countries, including the US and in the EU. APTIVUS, co-administered with ritonavir, is indicated for combination antiretroviral treatment of HIV-1 infected patients who are treatment-experienced and infected with HIV-1 strains resistant to more than one protease inhibitor.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.0 pM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
APTIVUS
PubMed

PubMed

TitleDatePubMed
Structure-based design of HIV protease inhibitors: sulfonamide-containing 5,6-dihydro-4-hydroxy-2-pyrones as non-peptidic inhibitors.
1996 Oct 25
Antiviral activity of the dihydropyrone PNU-140690, a new nonpeptidic human immunodeficiency virus protease inhibitor.
1997 May
In vitro combination of PNU-140690, a human immunodeficiency virus type 1 protease inhibitor, with ritonavir against ritonavir-sensitive and -resistant clinical isolates.
1997 Nov
Tipranavir (PNU-140690): a potent, orally bioavailable nonpeptidic HIV protease inhibitor of the 5,6-dihydro-4-hydroxy-2-pyrone sulfonamide class.
1998 Aug 27
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).
2013 Dec
P2' benzene carboxylic acid moiety is associated with decrease in cellular uptake: evaluation of novel nonpeptidic HIV-1 protease inhibitors containing P2 bis-tetrahydrofuran moiety.
2013 Oct
Substrate envelope-designed potent HIV-1 protease inhibitors to avoid drug resistance.
2013 Sep 19
Patents

Sample Use Guides

In Vivo Use Guide
Adults: 500 mg APTIVUS® (tipranavir), co-administered with 200 mg ritonavir, twice daily. Pediatric patients (age 2 to 18 years): Dosing is based on body weight or body surface area not to exceed adult dose.
Route of Administration: Oral
In Vitro Use Guide
Tipranavir inhibits the replication of laboratory strains of HIV-1 and clinical isolates in acute models of T-cell infection, with EC50 ranging from 0.03 to 0.07 µM (18-42 ng/mL)
Name Type Language
TIPRANAVIR
EMA EPAR   INN   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
Official Name English
TIPRANAVIR [WHO-DD]
Common Name English
3'-((1R)-1-((6R)-5,6-DIHYDRO-4-HYDROXY-2-OXO-6-PHENETHYL-6-PROPYL-2H-PYRAN-3-YL)PROPYL)-5-(TRIFLUOROMETHYL)-2-PYRIDINESULFONANILIDE
Systematic Name English
TIPRANAVIR [MART.]
Common Name English
TIPRANAVIR [EMA EPAR]
Common Name English
TIPRANAVIR [ORANGE BOOK]
Common Name English
APTIVUS
Brand Name English
TIPRANAVIR [INN]
Common Name English
TIPRANAVIR [VANDF]
Common Name English
TIPRANAVIR [MI]
Common Name English
Classification Tree Code System Code
NDF-RT N0000000246
Created by admin on Tue Mar 06 11:23:06 UTC 2018 , Edited by admin on Tue Mar 06 11:23:06 UTC 2018
EMA ASSESSMENT REPORTS APTIVUS (AUTHORIZED: HIV INFECTIONS)
Created by admin on Tue Mar 06 11:23:05 UTC 2018 , Edited by admin on Tue Mar 06 11:23:05 UTC 2018
WHO-VATC QJ05AE09
Created by admin on Tue Mar 06 11:23:06 UTC 2018 , Edited by admin on Tue Mar 06 11:23:06 UTC 2018
LIVERTOX 969
Created by admin on Tue Mar 06 11:23:05 UTC 2018 , Edited by admin on Tue Mar 06 11:23:05 UTC 2018
WHO-ATC J05AE09
Created by admin on Tue Mar 06 11:23:06 UTC 2018 , Edited by admin on Tue Mar 06 11:23:06 UTC 2018
NDF-RT N0000175889
Created by admin on Tue Mar 06 11:23:06 UTC 2018 , Edited by admin on Tue Mar 06 11:23:06 UTC 2018
Code System Code Type Description
RXCUI
190548
Created by admin on Tue Mar 06 11:23:05 UTC 2018 , Edited by admin on Tue Mar 06 11:23:05 UTC 2018
PRIMARY RxNorm
CAS
174484-41-4
Created by admin on Tue Mar 06 11:23:06 UTC 2018 , Edited by admin on Tue Mar 06 11:23:06 UTC 2018
PRIMARY
WIKIPEDIA
TIPRANAVIR
Created by admin on Tue Mar 06 11:23:05 UTC 2018 , Edited by admin on Tue Mar 06 11:23:05 UTC 2018
PRIMARY
PUBCHEM
54682461
Created by admin on Tue Mar 06 11:23:05 UTC 2018 , Edited by admin on Tue Mar 06 11:23:05 UTC 2018
PRIMARY SWITZERF
MESH
C107201
Created by admin on Tue Mar 06 11:23:05 UTC 2018 , Edited by admin on Tue Mar 06 11:23:05 UTC 2018
PRIMARY
HSDB
174484-41-4
Created by admin on Tue Mar 06 11:23:05 UTC 2018 , Edited by admin on Tue Mar 06 11:23:05 UTC 2018
PRIMARY
MERCK INDEX
M10885
Created by admin on Tue Mar 06 11:23:05 UTC 2018 , Edited by admin on Tue Mar 06 11:23:05 UTC 2018
PRIMARY Merck Index
ChEMBL
CHEMBL222559
Created by admin on Tue Mar 06 11:23:05 UTC 2018 , Edited by admin on Tue Mar 06 11:23:05 UTC 2018
PRIMARY
EVMPD
SUB04883MIG
Created by admin on Tue Mar 06 11:23:05 UTC 2018 , Edited by admin on Tue Mar 06 11:23:05 UTC 2018
PRIMARY
EPA CompTox
174484-41-4
Created by admin on Tue Mar 06 11:23:05 UTC 2018 , Edited by admin on Tue Mar 06 11:23:05 UTC 2018
PRIMARY
NCI_THESAURUS
C66603
Created by admin on Tue Mar 06 11:23:06 UTC 2018 , Edited by admin on Tue Mar 06 11:23:06 UTC 2018
PRIMARY
DRUG BANK
DB00932
Created by admin on Tue Mar 06 11:23:05 UTC 2018 , Edited by admin on Tue Mar 06 11:23:05 UTC 2018
PRIMARY
LactMed
174484-41-4
Created by admin on Tue Mar 06 11:23:05 UTC 2018 , Edited by admin on Tue Mar 06 11:23:05 UTC 2018
PRIMARY
INN
7774
Created by admin on Tue Mar 06 11:23:05 UTC 2018 , Edited by admin on Tue Mar 06 11:23:05 UTC 2018
PRIMARY